{[(1S,4R)-4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]cyclopent-2-en-1-yl]methoxy}phosphonic acid

• ChemBase ID: 158809
• Molecular Formular: C14H19N6O4P
• Molecular Mass: 366.312221
• Monoisotopic Mass: 366.12053975
• SMILES: n1c(nc2c(c1NC1CC1)ncn2[C@H]1C=C[C@H](C1)COP(=O)(O)O)N
• Canonical SMILES: Nc1nc(NC2CC2)c2c(n1)n(cn2)[C@H]1C=C[C@H](C1)COP(=O)(O)O
• InChI: InChI=1S/C14H19N6O4P/c15-14-18-12(17-9-2-3-9)11-13(19-14)20(7-16-11)10-4-1-8(5-10)6-24-25(21,22)23/h1,4,7-10H,2-3,5-6H2,(H2,21,22,23)(H3,15,17,18,19)/t8-,10+/m1/s1
• InChIKey: YQBOXVWMECPEJS-SCZZXKLOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[(1S,4R)-4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]cyclopent-2-en-1-yl]methoxy}phosphonic acid
• IUPAC Traditional name: abacavir monophosphate
• Synonyms: (1S,4R)- 4-[2-Amino-6-(cyclopropylamino)-9H-purin-9-yl]-2-cyclopentene-1-methanolDihydrogen Phosphate (Ester); (1S-cis)-Abacavir Monophosphate; Abacavir 5'-Phosphate

Database IDs

• CAS Number: 136470-77-4
• PubChem SID: 162252944
• PubChem CID: 469588

CALCULATED PROPERTIES

• Acid pKa: 1.6202377
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -2.1170034
• LogD (pH = 7.4): -2.818354
• Log P: -0.5158867
• Molar Refractivity: 93.496 cm^3
• Polarizability: 34.380135 Å^3
• Polar Surface Area: 148.41 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: White Solid
• Melting Point: 189-194°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - A105020

A metabolite of Abacavir (A105000).

REFERENCES

• Faletto, M., et al.: Antimicrob. Agents Chemother., 41, 1099 (1997)
• Hatse, S., et al.: Biochem. Pharm., 58, 311 (1997)
• Krejcova, R., et al.: Biochem. Pharmacol., 60, 1907 (1997)
• Holy, A., et al.: Curr. Pharm. Des., 9, 2567 (1997)